This invention relates to certain compounds in which a carbon atom of a pyrrolidine or piperidine ring is bonded directly or through a methylene group to the nitrogen of a substituted benzamido group, and their pharmaceutically acceptable salts. The benzamido group of these compounds is substituted by one to three 1,1-dihydroperfluoroalkoxy substituents. The compound and their pharmaceutically acceptable salts are active as antiarrhythmic agents. The invention also relates to certain novel intermediates and to processes useful to prepare the compounds.
Esters of benzoic acid substituted on the aromatic ring by 1,1-dihydroperfluoroalkoxy substituents are described in U.S. Pat. No. 3,655,728. Certain amides of benzoic acid substituted on the aromatic ring by 1,1-dihydroperfluoroalkoxy substituents are described in U.S. Pat. No. 3,719,687. The novel compounds of the present invention differ structurally from those disclosed in U.S. Pat. No. 3,719,687 in that (1) all of the compounds of the present invention are bonded to the benzamido nitrogen atom through a methylene group or carbon-nitrogen bond to a carbon of the pyrrolidine or piperidine ring, (2) the compounds may be either secondary or tertiary amines and (3) in the present invention only one or no carbon atoms link the benzamido nitrogen atom to a pyrrolidine or piperidine ring. Also, preferably and in most cases the compounds of the invention have an asymmetric center (i.e. carbon atom). The compounds of the present invention have, in general, an improved therapeutic ratio over the compounds of the prior art.